Development of new methods for glycosylation and syntheses of heterocycles containing sugar molecules
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Development of new methods for glycosylation and syntheses of heterocycles containing sugar molecules
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| Creator |
Dutta, Samrat
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| Subject |
Chemistry
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| Description |
The studies embodied in this thesis include the development of a new glycosylation method suitable for one-pot glycosylation strategies, and the synthesis of carbohydrate based heterocycles. The total work was carried out in the Department of Chemistry (Carbohydrate), CSIR-Indian Institute of Chemical Biology, Kolkata (India), under the planning and guidance of Dr. Asish Kumar Sen, Chief Scientist, of the same Institute. The thesis is broadly divided into two chapters. Chapter 1: This chapter is divided into two parts. Part A contains a brief review of the different methods for glycosylation developed in recent times. Some examples of synthesis of biologically active compounds along with references have been incorporated.Part B describes the use of iodine for efficient and chemoselective glycosylation using glycosyl ortho-alkynylbenzoates as donor. This glycosylation reaction can also be achieved selectively in presence of thioglycosides. This attribute was utilized for the synthesis of a manno-trisaccharide in one-pot condition. The introduction to the work, results and discussion, experimental procedures, conclusion, spectroscopic data and related references are included in this part. The work has been published in Tetrahedron Lett. 2013, 54, 865- 870.Chapter 2: This chapter is divided into three parts. Part A deals with a brief review of the recently developed methods used for the synthesis of triazoles, especially carbohydrate-triazole conjugates. The syntheses of some important biologically active compounds along with related references are also incorporated. Part B includes the one-pot synthesis of triazole-O-glycoconjugates and triazolyl glycoconjugates. The methodology combines a glycoylation and azide alkyne cycloaddition in one-pot to form triazole-O-glycoconjugates and triazolyl glycosides. The glycosylation reaction was promoted by silver triflate which also oxidized Cu(0) for the following cycloadditiion step. The introduction to the work, results and discussions, experimental procedures, conclusion, spectroscopic data and related references are included. Part C describes the one-pot synthesis of 1,2,3-triazoles linked chiral 2- substituted benzimidazoles. CuI used in the reaction procedure plays a dual role in promoting a aldehyde functionality for oxidative cyclization and activating a terminal carbon-carbon triple bond to undergo azide-alkyne cycloaddition. The introduction to the work, results and discussion, experimental procedures, conclusion, spectroscopic characterization data and related references are included. The work was published in J. Heterocyclic Chem. 2013, 50, 689-695.Finally, the list of the published papers and reprints are attached.
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| Date |
2013
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| Type |
Thesis
NonPeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2076/1/Thesis.pdf
Dutta, Samrat (2013) Development of new methods for glycosylation and syntheses of heterocycles containing sugar molecules. PhD thesis, Jadavpur University. |
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| Relation |
http://www.eprints.iicb.res.in/2076/
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